Advanced organic synthesis
Learning outcomes of the course unit
In recent past years, the discovery of novel and ever-sophisticated synthetic methods and techniques to access function-rich natural and non-natural organic molecules is an open field of inquiry, with wide impact on allied disciplines as bio-organic chemistry, medicinal chemistry, chemical biology, pharmacology, pharmaceutical technology.
On these premises, one main goal of this course is devoted to widening the basic knowledge on organic synthesis, by approaching chemical reactions and organic synthesis methods which were not mentioned in previous organic chemistry courses. The central themes of the course are intended to provide the student with a knowledge in the organic synthesis field which may be useful in the context of future professional engagement in the pharmaceutical and chemistry industry.
At the end of the course students are expected to have gained the following skills:
1. Knowledge and Understanding:
- To explain with useful examples the principles underlying advanced organic reactions allowing the rational interpretation of reaction mechanisms and understanding of similarities and differences among different reaction pathways
2. Applying Knowledge and Understanding
- To select information and ideas in order to make judgments and apply such information to solve ever emerging problems of organic synthesis, and to propose ways to design and synthesize simple chiral organic compounds.
3. Communication and Learning Skills
- To acquire learning skills and communication skills by employing appropriate language to both specialized and non-specialized audience, in line with the above mentioned objectives.
4. Making Judgements
- To critically review a synthetic strategy aimed at the preparation of a small, polyfunctionalized molecule.
To fully appreciate the content of the course, it is necessary to acquire knowledge of organic chemistry basics in previous courses. To access the final examination, it is necessary to pass the Organic Chemistry Basics/Organic Chemistry” exam (Pharmacy) or Organic Chemistry I (CTF), or similar organic chemistry courses.
Course contents summary
The following topics will be treated:
.Recall of basic carbon-carbon bond-forming reactions as gained by previous organic chemistry courses
.Recall of the frontier molecular orbital theory
.Thermal cycloaddition reactions (Diels-Alder reaction, 1,3-dipolar cycloadditions)
.Photochemical cycloaddition reactions
.Transition metal-catalyzed carbon-carbon bond-forming reactions
The following topics will be treated:
Recall of basic carbon-carbon bond-forming reactions as acquired by previous organic chemistry courses
Recall of the frontier molecular orbital theory
Thermal cycloaddition reactions (Diels-Alder reaction, inverse electron demand Diels Alder reaction, hetero-Diles Alder, Alder-ene, 1,3-dipolar cycloadditions with nitrones, azamethyne ylides, azides)
Photochemical cycloaddition reactions
Sigmatropic rearrangements (Claisen, Ireland-Claisen, Johnson, Cope, .)
Transition metal-catalyzed carbon-carbon bond-forming reactions (principles, Heck, Suzuki-Miyaura, Sonogashira and other cross-couplings)
Organocatalysis (principles, activation modalities, application in asymmetric synthesis, multicatalysis)
J. CLAYDEN, N. GREEVES, S. WARREN, "Organic Chemistry", Second edition, Oxford University Press 2012.
Materiale didattico integrativo:
Articoli scientifici consultabili nei database accessibili dall'Ateneo
Libri di testo per la consultazione:
1. Kurti Laslo, Czako Barbara "STRATEGIC APPLICATIONS OF NAMED REACTIONS IN ORGANIC SYNTHESYS", Academic Press, 2005.
2. Francis A. Carey, Richard J. Sundberg "Advanced Organic Chemistry. Part A: Structure and Mechanisms", Springer-Verlag; Fifth Ed. 2007.
3. Francis A. Carey, Richard J. Sundberg "Advanced Organic Chemistry. Part B: Reaction and Synthesis", Springer-Verlag; Fifth Ed. 2007.
According to the abovementioned objectives and contents, the course will be carried out through frontal oral lessons favoring active learning modalities using a heuristic-socratic approach, implying a dialogical relationship with the students. In the second part of each lesson, suitable exercises will be proposed dealing with the design, synthesis, and transformation of simple organic molecules which could be connected with the pharmaceutical and biological domains. These exercises are open for free discussion between teacher and students and they are considered an essential part of the course. Also several “case studies” will be analyzed following those criteria and methods described in the teaching and bibliographical material provided. All teaching slides will be uploaded weekly on Elly web-platform. All students willing to download the slides need to enlist first on the on-line course. These slides are considered to all intents and purposes important teaching material, as the books are. All not-attending students should always check on a regular basis the available material on the Elly-platform.
Assessment methods and criteria
The final examination consists of a written exam dealing with the execution of exercises on the synthesis and reactivity of organic compounds. This test is aimed at verifying whether the student has developed the skill and ability of selecting and deploying information from the theory study in order to furnish solutions to a given practical organic chemistry problem. The result of the written exam is marked as optimum, good, adequate, inadequate. A minimum of adequate is required as a threshold.